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Deputy Chief of Protocol Dennis Cheng (right) greets former British Prime Minister and Quartet Representative Tony Blair upon arrival at the State Department in Washington for a meeting with Secretary of State Hillary Rodham Clinton on Aug. 31, 2010. (Associated ... more >

Throughout their time in the spotlight, Bill and Hillary Clinton have been dogged by questions about a blurred line between political fundraising and official actions. From Buddhist monks, White House coffees and the Lincoln Bedroom to fundraising bundlers and Whitewater investment partners who went to prison, the questions have persisted for two decades.

Mrs. Clinton’s impending second run for president in 2016 opens a new chapter in that saga, as questions mount about the connections between her husband’s massive private Clinton Foundation fundraising and her work as the secretary of state.

The scrutiny has already piqued interest in a fresh example of a fundraising revolving door through which a long-trusted aide has passed.

Dennis Cheng was a key fundraiser for Mrs. Clinton’s successful campaign for Senate and her 2008 presidential campaign, then followed her to the State Department, where he served as a key gatekeeper for foreign dignitaries and heads of state who sought visits with the president and secretary of state.

After two years as the deputy chief of protocol at State, Mr. Cheng moved to the Clinton Foundation to serve as its chief of development, essentially the chief fundraiser. And now many expect he is leaving the foundation to become a key player in Mrs. Clinton’s next campaign.

“He’s a very interesting actor in the relationship, with his role at the Department of State and then raising money from foreign leaders and countries at the foundation,” said Matthew G. Whitaker, a former U.S. attorney from Iowa who now runs the watchdog group the Foundation for Accountability and Civic Trust (FACT).

“As a former prosecutor, we need to conduct our investigation before we draw any conclusions. But we are interested in what his role might have been,” he added.

FACT last week drew attention to Mrs. Clinton’s use of a private email account at the State Department, demanding a formal Justice Department probe. This week it filed a request for all records from State detailing Mr. Cheng’s work and contacts at the agency.

State Department officials declined to provide The Washington Times any information on Mr. Cheng’s day-to-day activities at State or whether he had contacts with the agency after he left.

The Clinton Foundation has been rocked by charges of influence in the last several weeks following a Wall Street Journal report that it had taken money from such regimes as those in Saudi Arabia, the United Arab Emirates and Algeria, albeit mostly after Mrs. Clinton’s tenure as secretary of state. While she was America’s chief diplomat, the foundation banned foreign contributions.

To date, no one has made any suggestion of any wrongdoing. But curiosity is rising, and even Clinton insiders acknowledge the revolving door story will likely raise questions about appearances, even as they describe Mr. Cheng as a trusted, reliable aide whose work at the foundation focused on helping poor citizens across the globe.

“Despite what the optics may be — that Mr. Cheng used to work at the State Department — he’s now working for the foundation doing good for countries around the world, whether it’s combatting cholera in Haiti or HIV in Africa. There’s really nothing wrong here, only good works,” said a source close to the Clinton Foundation, who spoke only on condition of anonymity.

Melanie Sloan, a former federal prosecutor and longtime ethics watcher in Washington, said that she saw nothing wrong in Mr. Cheng’s placement at State, but acknowledged that, in retrospect, it could draw more fire to Mrs. Clinton.

“The Clintons are very insular and like to keep the same people around them, so it’s not a surprise to have the same people around her,” Ms. Sloan told The Times. “You bring your people from one thing to the next, and many of these people, their entire careers are based on being a staffer to the same ever-rising politician. It’s just not unique, it’s the well-worn path.

According to his official biography, Mr. Cheng served as Mrs. Clinton’s New York finance director from 2005 to 2008 for her Senate and presidential campaigns and later held the position of chief development officer for the foundation.

“As Deputy Chief, Mr. Cheng serves as Acting Chief of Protocol in the absence of the Chief,” the site said. “In this role, Mr. Cheng oversees the visits of heads of state, chiefs of government and other international dignitaries who are in the United States to meet with the President, Vice President or Secretary of State. Additionally Mr. Cheng supervises the management, administration and budgetary matters of the office.”

Mr. Cheng reportedly helped raise $248 million for the foundation during his tenure from 2011 to 2013 and earned over $200,000 annually.

His background as an experienced campaign fundraiser also stands out since the deputy chief of protocol position almost exclusively involves scheduling and spending time accompanying foreign dignitaries on their visits to the U.S.

“The gatekeeper to the president for foreign governments is the U.S. secretary of state. They make the recommendation to the president on who we should speak to and how much time they should be afforded, and the secretary’s chief of protocol is the one who implements all of that,” said Bradley Blakeman, who served from 2001 to 2004 as deputy assistant to the president for appointments and scheduling, vetting and research, correspondence and surrogate scheduling.

“Obviously you’d want someone in that position who has a scheduling and advanced background or someone with administrative skills, because that office is all about managing time and staff. There’s no fundraising involved at all — at least there isn’t supposed to be,” Mr. Blakeman said.

Mr. Cheng’s predecessor, Charity Wallace, had such a background as Mr. Blakeman described. She formerly served as director of advance for then-first lady Laura Bush before taking the deputy chief of protocol position.

Ms. Wallace “was responsible for the execution of Mrs. Bush’s 300-plus annual events outside the White House and served as her primary negotiator and protocol and logistics advisor for all foreign trips as well as domestic visits. During her tenure, [Ms.] Wallace traveled to more than 60 countries, working with foreign leaders and officials and Embassy staff from around the world,” according to her LinkedIn profile.

“Prior to joining the U.S. Department of State, Mr. Cheng served as National Finance Director for then-Senator Hillary Rodham Clinton. From 2005 to 2008, he served as New York Finance Director for her Senate and Presidential campaigns. He has also served on the campaigns of Senator John Kerry, General Wesley Clark, Congresswoman Doris Matsui and New York Attorney General Andrew Cuomo, and as a consultant to the William J. Clinton Foundation,” according to the department.

Mr. Cheng’s background has also not gone unnoticed by the media.In September, Politico reported that, “The person seen as the likeliest to have a major finance role [in Mrs. Clinton’s 2016 campaign] is Dennis Cheng, who is currently the main fundraiser at her family’s foundation.”

On Feb. 13 The Washington Post wrote, “The overlap between the Clintons’ political network and their charitable work was apparent Friday, when Dennis Cheng stepped down as the foundation’s chief development officer ahead of his expected role as a key fundraiser for Clinton’s 2016 campaign.”

Mr. Blakeman said that he was not surprised to learn Mrs. Clinton placed an experienced fundraiser from her campaign in the position of deputy chief of protocol.

“They coordinate the arrivals of heads of state and, in some instances, cabinet members. The chief of protocol is the official host,” Mr. Blakeman explained.”They handle all their needs and wants while they’re here. They are the official welcome wagon of the president, they do all the facilitation. They will accompany heads of state and dignitaries if they take side trips around the country. What better person to schmooze with a potential contributor than a fundraiser.”